


You Know I’m No Good

by outoftheashes



Category: Supernatural
Genre: Abrupt Ending, Addiction, Alcoholic Dean Winchester, Anal Fingering, Anal Sex, Angst, Banter, Barebacking, Blow Jobs, Bottom Sam, Cheating, Guilt, Incest, Infidelity, M/M, Prompt Fill, Shame, Sibling Incest, Smut, Spit As Lube, Top Dean Winchester, Top Dean Winchester/Bottom Sam Winchester, Unhealthy Relationships, come suffer with me, i was just trying to write kink but angst got in the way of my boner, mentioned Sam/Jess, please don't murder me over the ending, sam cheats on jess with dean, smut and pain
Language: English
Status: Completed
Published: 2020-08-24
Updated: 2020-08-24
Packaged: 2021-03-06 16:21:11
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,273
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26091787
Author URL: https://archiveofourown.org/users/outoftheashes/pseuds/outoftheashes
Summary: Dean gives Sam a small smirk and leads the way into his home. There’s porn on the living room coffee table and an ashtray with a smoldering cigarette. Sam stares at the cigarette until Dean hands Sam an open beer. "What did you wanna talk about, little brother?""Shit." Sam fumbles with the beer, spilling some on his hand. He takes a sip and clears his throat as he desperately tries to find his footing. "Well... You know how things are with Jess," Sam starts awkwardly. God, he could kick himself.**Inspired by the prompt:What Is And What Should Never Be AU. Dean is Sam’s no good big brother who flunked out of school, steals their mom’s silver to pay off his gambling debts, and is drunk more often than not. And he fucks Sam like no one else ever does. And Sam can’t bring himself to put a stop to it, even after he asks Dean to be his best man at his wedding to Jess.
Relationships: Dean Winchester/Sam Winchester
Comments: 31
Kudos: 113
Collections: SPN_Masquerade Spring 2020





	You Know I’m No Good

**Author's Note:**

> Written for spnmasquerade 2020. Finished it months ago and posted it on lj but didn’t manage to throw it up on ao3 until now. 
> 
> I was just trying to write some kink but angst got in the way of my boner, so now you lot get to suffer with me. Or you can skip the second scene and pretend it ends sweetly? I won’t judge you (much) if you ignore the last bit. ;D 
> 
> I didn’t think to include Carmen. In part due to the prompt but it also entirely slipped my mind. So I guess Dean isn’t dating her yet, she doesn’t exist in this au, or Sam doesn’t know about her. Whatever option works for you. 
> 
> Also, yeah, you caught me. I was totally listening to Amy Winehouse while editing this fic, which led to the title.

Sam taps his knuckles against Dean's door, knowing full well he shouldn’t _be_ here. He shouldn't be asking Dean anything at home. They should do this with family. Publicly. _Anywhere_ else.

But he can never seem to bring himself to stop.

The door swings open and Dean brightens, a bottle of beer in hand. "Hey, Sammy. What can I do for you?"

"We made plans to see each other about a week ago. I sent you a reminder message this morning. Should we reschedule?"

Dean's forgetfulness is a small price to pay considering what Sam’s doing to Jess. To himself. To the whole family, really. Sam deserves this and so much more.

Dean licks his lips and his eyes glide along Sam’s body, a gentle caress. "Didn’t get it, my phone’s dead. But you can come in. Want a beer?"

Sam stays rooted to the spot, eyes on Dean's mouth. "I guess.”

Dean gives Sam a small smirk and leads the way into his home. There’s porn on the living room coffee table and an ashtray with a smoldering cigarette. Sam stares at the cigarette until Dean hands Sam an open beer. "What did you wanna talk about, little brother?"

"Shit." Sam fumbles with the beer, spilling some on his hand. He takes a sip and clears his throat as he desperately tries to find his footing. "Well... You know how things are with Jess," Sam starts awkwardly. God, he could kick himself.

"Jess? Oh yeah. Jess. The sexy blonde thing you’re dating. Yeah, what about her?"

"Dude." Sam shakes his head, letting out an annoyed huff. It’s so easy for Dean to get under Sam's skin. A goddamn skill that no one else can replicate. Dean is in a league of his own. "We're not dating. It's way more than that. And... She's not a thing, Dean."

Dean shrugs. "So, are you gonna tell me or what?" There’s a flash of victory in Dean’s eyes. Probably because he knows he’d annoyed Sam.

"We're getting married. And I wanted to know if you'd be my best man."

Dean stares at Sam a moment then starts to laugh. "You want the guy you're fucking, your side piece, to be your best man? That's rich, Sammy. I'll do it. I'll do it cause I love you so damn much but Christ that's funny."

"Jerk." Sam's chest squeezes painfully at Dean's laugh. His eyes dance around the living room before landing on Dean's face. "It's not funny. It's the truth. It's how I feel and what I want. If you don't want to, that's fine. But I can't see myself asking anyone else."

"I already said I'd do it,” Dean tells Sam. "And that's... That's real touching,” Dean adds and it almost feels genuine. A rare moment of softness.

"Okay." Some tension melts out of Sam. He takes a few sips of beer and nods. "Want me to stay or should I leave?"

"You're always welcome here." Dean goes to the couch and tosses an empty pizza box towards the kitchen and sits, patting the seat beside him.

"Always, huh?" Sam obeys, melting into the couch, into Dean's side.

Dean puts his arm up on the couch behind Sam's shoulders. "That's what I said." He runs his thumb along Sam’s jawline, mouth slightly open as he eyes him. "It's a mistake marrying her. Unless you're breaking up with me. You breaking up with me, baby brother?"

"I -" Sam pauses, letting out a soft, almost desperate noise. "What do you think?"

"I think Jess doesn't fuck you like I do. Does she even peg you anymore? Being a married man and all, not being able to get away as easy... Jesus, when you show up you'll be aching. Begging for my cock." Dean bites his lower lip and looks over at Sam through his lashes. "Tell me I'm wrong."

Dean has to know the answer already, he’s a smug, confident asshole - but he’s asking anyway. Because he wants to _hear_ it. He always wants to hear it. "You aren't," Sam all but whispers, his body singing with pleasure. It’s alive now. Waiting for Dean to make a move. "You know you aren't wrong."

Dean runs his hand down his thigh and pats it. "So why don't you come over here and sit in my lap?”

Sam swallows thickly. "Maybe I just want your companionship, Dean. Ever think of that?"

In general, that might be accurate. Right now, though -

"Liar,” Dean accuses, completing Sam’s inner thoughts. "I _know_ you, Sammy. I know that look on your face."

"Just because I want you doesn't mean anything needs to happen.”

"So I was right,” Dean says. Like it’s the only thing that matters. At this moment, Sam supposes that’s true enough. Dean smirks and manhandles Sam into his lap.

"You're so stubborn," Sam says, squirming at their proximity. He doesn’t try to extricate himself from Dean’s grip.

Dean squeezes Sam’s ass. "I know what I want and I take it.”

"Obviously," Sam says, dragging his fingers along Dean's cheeks. "You don't feel bad.”

"Not. A. Bit,” Dean tells him between kisses, his fingers tightening on Sam's ass.

Sam's dick twitches in his jeans as he returns Dean's kisses. "I wish I could be more like you."

Dean lifts one of his hands to Sam's mouth. "Why's that?"

Sam kisses Dean's fingers one by one. "Because of what we're talking about," he snarks. "Come on, dude. Keep up."

"You mean you wish you didn't care that you’re here, in your brother's lap, sucking his fingers while your fiancée is waiting for you to come home?" Dean purrs, his breath ghosting along Sam’s face.

"I'm not sucking your fingers," Sam says and nips Dean's thumb. His dick perks at Dean's purring, a fucking Pavlovian response. His dick is aware of this song and dance, it knows what’s next on the agenda. "How do you manage it? Not caring?"

"Now you'll suck them." Dean slides his fingers into Sam's mouth. “I don't care because you’re _mine_ , sweetheart.”

Sam caresses his tongue along Dean's thick fingers and sends him a cranky look but there’s no real heat involved. While Sam sucks, Dean undoes Sam's jeans with his free hand. When his fingers are nice and slick, he presses his hand down the back of Sam's pants and grazes his hole, teasing. "Glare at me all you want. I'd know you were hard right now even if I couldn't feel it."

"Bastard," Sam pants against Dean's lips and gives them a quick bite. "Yeah, I'm hard. And I know that you know. I'm not exactly subtle when I'm turned on, am I? Just... be careful. No marks."

Dean nips at Sam's jawline and sinks into his ass. "Or what?"

"Or I'll kick your ass," Sam hisses, taking Dean's finger deeper inside. It’s an empty threat but it’s his duty as the younger brother to mention it. "Or I'll leave you here with blue balls. No hickeys, Dean."

"But you're mine." Dean licks the sensitive flesh of Sam’s throat and he _knows_ down to his bones it’s where Dean wants to bite. “Just a little one, c’mon. Want you.”

"I said no," Sam replies as firmly as he can manage. "Besides, I already know I'm yours. I don't need a mark to prove that."

"I'll be a good boy since you’re being so bad for me,” Dean says as he slides another finger into Sam and starts scissoring them.

Being called 'bad' shakes something loose in Sam and he attacks Dean's mouth with a needy groan.

"Mm, there we go.” Every few strokes Dean’s hips jerk upwards, his thick cock obvious through his pants.

"What's got you so desperate tonight, Dean?" Sam asks, breathing into Dean's ear. "You keeping something from me?"

"I can't be turned on by my little brother?"

Sam laughs at the ridiculousness of Dean's question. "Most people would say no."

"We aren't most people."

"That's certainly true.”

Dean works in finger number three, dragging his teeth across Sam's jawline. "I can't wait to bury myself deep inside you, Sammy. It's been too long."

"It has," Sam admits and buries his face in Dean's neck, hiding his eyes from Dean's scorching hot gaze. "Do I get to suck you off first?"

Dean moans, his fingers curling against Sam's prostate almost desperately. "Well, when you ask me so sweetly."

"You know you love it, has nothing to do with me asking," Sam says. He’s aching. It honestly hurts. But it’s a hurt he deserves. A penance. Or the start of one, at least.

"I love it when you ask,” Dean breathes. "So fucking hot." He bites Sam's ear lobe.

"I love it when you take," Sam tosses back, grinding on Dean's fingers.

Dean smacks Sam's ass hard. "Up. I want you on my bed.”

"Not yet. Wanna taste your dick first."

"Well, you know where the floor is,” Dean says, pulling his fingers from Sam's hole.

"Jerk," Sam huffs and slides off of Dean's lap, plopping down on the ground gracelessly. He gazes at Dean a few heartbeats before nuzzling at Dean’s crotch, his entire body shaking.

Dean runs his hand through Sam's hair and tugs. "Go on, bitch. Take it out."

Sam lets out a soft noise at the rough treatment and slowly does as asked, his tongue darting out of his mouth eagerly as he unzips Dean's pants and pulls his cock free.

Dean presses a thumb into Sam's mouth and Sam flicks his tongue against Dean's finger suggestively, eyeing Dean through his lashes.

"Christ,” Dean gasps. "I'll never get over how fucking pretty you are." He stares a few moments before pulling Sam's mouth down on his cock.

Sam gags before relaxing his throat and breathes deeply through his nose. He drags his tongue along the underside of Dean's cock, slow and worshipful, enjoying the salt and weight of him.

Dean groans, his fingers tightening in Sam's hair. "This’ll keep you coming back. Jess can make you gag on a plastic cock but it’s not the same as the real thing now, is it?"

It isn't. He's tried, he honestly has. But there’s no contest. Dean always fucks him just right, touches places Jess never can. Sam nods in agreement and sucks on Dean slow and messy.

Dean's head falls back on the couch. "That's nice, Sammy... I love it. You're always so eager. Such a good little cock sucker."

Sam bobs his head a few times before pulling off and kisses the tip of Dean's cock. "I'm sure you say this to everyone."

Dean chews on his deliciously plump lips. "I say nice things, sure. But not like this. I've never had anyone suck me quite like you."

"I'm not _that_ great at it," Sam says, laughing softly and gives the tip of Dean's dick a gentle suck.

Dean groans, pushing Sam further down on his cock. "Yes, you are."

Sam lets out a muffled whine around Dean's cock and starts slowly bobbing his head once more, his hole clenching on nothing each time Dean's dick plunges inside his mouth.

Dean lets Sam work him for a minute or two. "I'm gonna come if you don't stop," he pants, reaching down to squeeze his cock at the base. "Time for you to get naked for me."

Sam nods and pulls his shirt off while on his knees without complaint. "Still want me on your bed?" he asks, licking his lips.

"Yeah.” Dean smirks. "Can't have you getting rug burn.”

"You don't care," Sam disagrees. He stands up and begins to free himself of his pants. "There's another reason."

Dean keeps squeezing his cock as he watches Sam. "Might be," he says softly, like a secret.

Once he’s completely naked, Sam holds out a hand to his brother. "Come on."

Dean follows Sam, pulling off his clothes on the way and smacks Sam's ass. "Face down, ass up."

Sam obediently lays out on the bed. "Someone's desperate. And by someone I mean you."

"Like I've said... It's been a while." Dean kneels on the bed behind Sam, making it creak and complain. He spreads Sam's cheeks and licks into his hole without warning.

"Fuck," Sam says roughly, rubbing his face against the bed as he rocks against Dean's face. "I thought you were gonna shove your dick in me. This might be better."

"I know how sensitive your pretty little hole is," Dean purrs and goes back in, sucking on him.

"Asses aren't pretty, Dean," Sam says as precome drips from his cock.

"Mm, yours is. Wanna pass me the lube?”

"I don't need it. You can take me right now," Sam offers, wiggling his ass. “Don't you wanna get in me? Why wait? Why waste time?"

“You wanna _feel_ it after, hmm?" Dean shifts, lining up his cock with Sam's hole. "Wanna go home and kiss your fiancée with your ass aching from my cock?"

"Yes. Don't _you_ want that?"

"I want everything you have to give,” Dean hisses. His fingers tighten on Sam's hips and he starts to sink into Sam.

"Dean."

"Come on, wanna hear you beg,” Dean says and thrusts in brutally which is _good._ Sam doesn’t want mercy.

"What exactly am I supposed to be begging for?"

"For me to fuck you. Hard.”

"I don't think so," Sam says, meeting Dean’s thrusts. "What are you gonna do if I don't? Stop? You wouldn't deny yourself like that."

Dean slows his movements and pulls back until only the head of his cock is inside. "I'll just take it nice and easy."

Sam snakes a hand beneath himself and begins stroking his cock. "Go for it." His hole clenches greedily, wanting and needing more but he isn't going to give Dean the satisfaction of begging.

Dean spanks Sam's ass. "No touching."

Sam yelps and slows his strokes but doesn’t pull his hand away. "Or what? You'll spank me some more?"

"Damn right I'll keep spanking you."

"Fine." Sam groans in frustration and after a few final strokes he lets go of his cock. "There. Happy now?"

"Yes." Dean continues his tortuously slow movements. Sam lets out a soft growl and meets Dean's glacial thrusts.

It doesn’t take long for Dean to lose patience and start pounding Sam harder. Dean isn’t known for having impulse control. Quite the opposite. Impulsive and reckless. That’s Dean.

Sam isn’t much better, though.

"Knew you'd break. You love my ass too much."

"Do you blame me? Sweetest fucking ass I’ve seen,” Dean pants.

"I don't." Sam looks over his shoulder so he can gaze at his brother. God, he’s beautiful. It’s fucking terrifying. "That why you want my ass in the air? So you can watch it the whole time? Pervert."

Dean spreads Sam's cheeks wider, watching his cock disappear inside Sam. "Yeah. That's exactly it."

"That's really hot," Sam admits quietly, his eyes still firmly on Dean and what he’s doing. There is nothing quite like the pure hunger in his eyes, the desperation in his body, and the rough quality of his voice.

"Guess you're a pervert too then, bitch." Dean chuckles and his hands return to Sam’s hips.

"Maybe a little.”

"You getting close? You gonna come by my cock alone?"

Sam shivers and wets his lips. "Kiss me and I might."

Dean obliges, his kisses hungry. Sam kisses Dean back with all the passion that had built up from the months they’d been separated and promptly makes a mess on Dean's bed. Dean quickly follows, crying out Sam's name and Sam moans as Dean fills him up, shaking with the effort to keep his ass in the air and not dissolve into a puddle.

Dean scrapes his nails along Sam's scalp, before pulling his softening cock out of Sam.

Sam spreads his ass so Dean can watch the come drip out. "How do I look?"

"Like the prettiest boy in a porn mag." Dean flicks his tongue against Sam’s messy hole.

"Fuck. Well at least I know I've got a solid backup career if current plans fall through.”

"Or you could move in with me,” Dean growls and keeps licking.

"What? Can't stand the thought of another man fucking me?" Sam asks, keeping his tone light and teasing.

"I can barely stand the thought of _Jess_ fucking you."

"So jealous," Sam says, his breath hitching, betraying how much he likes Dean's response.

Dean abandons Sam's ass and crawls up Sam’s body, kissing him when he’s close enough. "You love it."

_Always._

* * *

He’s still in Dean’s bed an hour later. He hadn’t meant to stay. He never does. And now his mind is swirling with another impossible conversation he needs to have with Dean. It’s not a good time. It’ll never be a good time. But it’s necessary. It’ll eat him up inside if he pretends he didn’t see and doesn’t know.

"Hey, can I ask you something?"

"What?"

Sam runs his fingers along Dean's arm and takes a deep, cleansing breath. "I know you've been stealing from Mom. I wanted to ask you to stop. If you need anything, come to me. I'll... I'll do my best to help."

"Like I'd go to my _baby_ brother for a fucking hand out," Dean says, irritation seeping into his tone as he rolls off the bed, putting distance between them.

Sam frowns and sits up. "Dean, that doesn't make any fucking sense. I’d help you _willingly_ , you don’t need to steal. Whatever’s going on with you -”

"You had better stop the fucking accusations, Sam."

"You're mad, I get that. But it happened. We can deal with this, Dean. Together. You don’t need to suffer alone.”

"You just said that you _think_ I'm stealing from Mom. You’ve got some nerve coming over, having sex with me, and then pulling out _that_ bullshit."

"Dude." Sam clenches his hands in the sheets on Dean's bed. "I said I _know_ you're stealing. I didn't say _think_. Know and think are two different things and I _know_ you are. Also, you already basically admitted it so get your fucking story straight."

"You don't know anything. You stopped knowing anything about me when you started dating that blonde bitch."

"Excuse you?" Sam gets off the bed and into Dean's space. "Jess has been nothing but nice to you, show some fucking respect."

"Why the fuck should I? You and me were perfectly fine before she came along," Dean replies, raising his chin in defiance.

"You know, there's only so much toxic bullshit I can handle, Dean," Sam says, spreading his arms out wide. “I don’t wanna leave but I will if you keep talking about Jess like that.”

Dean puts his hands on Sam's chest and pushes hard. "Toxic? _Toxic? You_ are the one who decided to ruin the moment by bringing up _untrue, bullshit_ accusations." He shoves Sam again.

"I saw you take mom's silver. What do you have to say to that?"

Dean grits his teeth and clenches his fists. For a brief moment, Sam thinks he’s about to get punched but Dean turns at the last second, sending his fist through the drywall. He shakes the dust off his hand and storms out of the room.

"You need help," Sam calls after him. He means rehab. Therapy. Self-help books. Something. Anything. "You really need help," he says again, this time barely above a whisper.

He wants to save Dean from his demons, take away his pain -

But Sam can’t.

And Dean? Dean won’t take his hand. He’d rather drown.

And Sam would rather sink beneath the waves with Dean than try to save himself.

**Author's Note:**

> So, I know the ending seems pretty bleak. Not sure if this makes it better or worse, but the boys will kiss and make up. Whether Dean takes Sam up on his offer and lets him help I have no clue but in my head, these two are stuck in a cycle. They might take time apart but it won’t last. 
> 
> If you’ve followed me for a while, you probably know I don’t post fics about infidelity. It’s not my strong suit and I have the sneaking suspicion I didn’t give the prompter what they wanted - but oh well. I tried. And, more importantly, I stepped outside of my comfort zone and did something new-ish for me. 
> 
> One last thing - I didn’t touch on it in the fic but Dean stole due to gambling debts, just like what was mentioned in the prompt. Do with that what you will. 
> 
> Anyway. 
> 
> Comments and kudos feed me!


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